Amphotericin B

Synonyms: NSC 527017

Amphotericin B (AMB, NSC 527017) is an amphipathic polyene antibiotic which permeabilizes ergosterol-containing membranes.

Amphotericin B  Chemical Structure

Amphotericin B Chemical Structure

CAS No. 1397-89-3

Purity & Quality Control

Amphotericin B Related Products

Biological Activity

Description Amphotericin B (AMB, NSC 527017) is an amphipathic polyene antibiotic which permeabilizes ergosterol-containing membranes.
Targets
ergosterol [1]
In vitro
In vitro Amphotericin B administration is limited by infusion-related toxicity, including fever and chills, an effect postulated to result from proinflammatory cytokine production by innate immune cells. Amphotericin B induces signal transduction and inflammatory cytokine release from cells expressing TLR2 and CD14. [1] Amphotericin B interacts with cholesterol, the major sterol of mammal membranes, thus limiting the usefulness of Amphotericin B due to its relatively high toxicity. Amphotericin B is dispersed as a pre-micellar or as a highly aggregated state in the subphase. [2] Amphotericin B only kills unicellular Leishmania promastigotes (LPs) when aqueous pores permeable to small cations and anions are formed. Amphotericin B (0.1 mM) induces a polarization potential, indicating K+ leakage in KCl-loaded liposomes suspended in an iso-osmotic sucrose solution. Amphotericin B (0.05 mM) exhibits a nearly total collapse of the negative membrane potential, indicating Na+ entry into the cells. [3]
In Vivo
In vivo Amphotericin B results in prolonging the incubation time and decreasing PrPSc accumulation in the hamster scrapie model. Amphotericin B markedly reduces PrPSc levels in mice with transmissible subacute spongiform encephalopathies (TSSE). [4] Amphotericin B exerts a direct effect on Plasmodium falciparum and influences eryptosis of infected erythrocytes, parasitemia and hostsurvival in murine malaria. Amphotericin B tends to delay the increase of parasitemia and significantly delays host death plasmodium berghei-infected mice. [5]
NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT05593666 Recruiting
Primary Visceral Leishmaniasis
Drugs for Neglected Diseases|Novartis Pharmaceuticals
December 27 2022 Phase 2
NCT05108545 Unknown status
Neutropenia and Fever
CSPC ZhongQi Pharmaceutical Technology Co. Ltd.
December 15 2021 Phase 3
NCT04993222 Completed
Bioequivalence
CSPC Zhongnuo Pharmaceutical (Shijiazhuang) Co. Ltd.
June 4 2020 Phase 1
NCT03905447 Terminated
Aspergillosis|Lung Transplant Infection
Pulmocide Ltd
September 17 2019 Phase 2
NCT03828773 Recruiting
Candidiasis|Fungal Infection|Acute Myeloid Leukemia|Genetic Predisposition|Aspergillosis
Bochud Pierre-Yves|Swiss National Science Foundation|Centre Hospitalier Universitaire Vaudois
February 11 2019 Not Applicable

Chemical Information & Solubility

Molecular Weight 924.08 Formula

C47H73NO17

CAS No. 1397-89-3 SDF Download Amphotericin B SDF
Smiles CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(C(CCC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O
Storage (From the date of receipt)

In vitro
Batch:

DMSO : 4.5 mg/mL ( (4.86 mM) Moisture-absorbing DMSO reduces solubility. Please use fresh DMSO.)

Water : 4.5 mg/mL

Ethanol : Insoluble


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In vivo
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

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Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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